Berricle Pearl Earrings (c/o) / Kate Spade Sunnies (Old, newer styles here) / DUO Riding Boots (c/o) / Henri Bendel Tote (c/o) / J.Crew Pocket Sweater (Different colors here, similar style here) / Legwear Loft Faux Leather Leggings (c/o) / Cinco Powell Tag and Chain (c/o) / Daniel Wellington Watch (c/o)

I’m sure I’ve mentioned this before, but large, dangly earrings freak me out. I love how they look on other people, and I’m constantly admiring them in stores and online. But they’re not for me. I’m terrified that they’ll stretch out my already large holes, or that I’ll end up with split earlobes. (It happened to a family member when I was younger, and she had to have them stitched up… so I guess her experience traumatized me!)

Hoytie Toity Designs Bow Flats (c/o — Take 10 percent off with code “KELLY10”) / Hudson Jeans (Best jeans ever.) / J.Crew Blazer, Shirt (Last seen here, but I’m obsessed with this new one!), Necklace and Earrings (Oops. Sometimes it just happens, you know?) / Madewell Tote (See other styles here, and J.Crew’s version here! Tip: The Madewell Transport Tote almost never goes on sale. However, Shopbop carries it, and Shopbop does have sales. Wait for one! Then bring your tote to a Madewell store during one of the brand’s “free monogramming” events. #worthit) / Daniel Wellington Watch (c/o) / Kate Spade Sunnies (Old, newer styles here)

A few weeks ago, I grabbed coffee at Floriole, an adorable coffee shop in Lincoln Park, with Cynthia from Sensibly Sharp. (She’s an Atlanta native, but was in town for business.) It was my first time meeting her, but she and I gabbed incessantly for over two hours… which was so nice. At the time, I was feeling a little down in the dumps, and I was missing home like crazy. Hanging out with Cynthia was awesome, though, and for a couple of hours, I completely forgot about everything I was sad about. Isn’t it wonderful when you connect with people so incredibly quickly? :) Thank you, Cynthia! It was lovely meeting you, and you’re such a sweetheart.

Duo Boots (c/o) / J.Crew Blazer (Wait for a sale!), Hat (Old, similar here, here, here and here) and Earrings / LuLu’s Scalloped Dress (c/o) / Kate Spade Bag (Old, but there’s a Kate Spade surprise sale going on right now!) / Daniel Wellington Watch (c/o) / Emma McKinstry Bracelet (c/o) / Hazel & Marie Pearl Bracelet (c/o) / I Love Jewelry Necklace (c/o — open pendant & charm)

This year, I decided to go all out and buy a pair of Tory Burch riding boots I’d fallen in love with. Expensive? Yes. But I waited for a killer sale, sold a bunch of stuff on eBay to help justify the purchase, and had a coupon code and gift certificate to use. I also promised myself that these would be my riding boots for the long haul; that I’d take care of them and get them re-soled when needed. After three months of hovering my cursor over the “order” button, I finally pulled the trigger.